isoquercetin
isoquercetin, enzymatically modified
Identification
| Name | isoquercetin |
| IUPAC | 3-[(2S,3R,4R,5R)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one |
| CAS Number | 21637-25-2 |
| EINECS | 244-488-5 |
| FDA UNII | 0YX10VRV6J |
| Molecular Formula | C21 H20 O12 |
| Molecular Weight | 464.38080000 |
| MDL Number | MFCD00017746 |
| Nikkaji Number | J11.252F |
| Beilstein | 0100989 |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | GRN 220 |
| FEMA Number | 4225 |
| FDA | No longer provide for the use of these seven synthetic flavoring substances |
| FDA Mainterm (SATF) | 977187-64-6 ; ISOQUERCITRIN, ENZYMATICALLY MODIFIED |
Physical Properties
| Appearance | white to dark yellow powder (est) |
| Assay | 97.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 226.00 to 228.00 °C. @ 760.00 mm Hg |
| Boiling Point | 916.00 to 917.00 °C. @ 760.00 mm Hg |
| Flash Point | 612.00 °F. TCC ( 322.22 °C. ) |
| logP (o/w) | 0.049 (est) |
| Shelf Life | 12.00 month(s) or longer if stored properly. |
| Storage | refrigerate in tightly sealed containers. |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | antioxidants |
No sensory data available
Safety Information
| European information | Most important hazard(s): |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | antioxidants and preservatives |
| Recommendation for isoquercetin usage levels up to | not for fragrance use. |
| baked goods | - |
| beverages(nonalcoholic) | 150.00000 |
| beverages(alcoholic) | 150.00000 |
| breakfast cereal | - |
| cheese | - |
| chewing gum | 1500.00000 |
| condiments / relishes | - |
| confectionery froastings | - |
| egg products | - |
| fats / oils | - |
| fish products | - |
| frozen dairy | 150.00000 |
| fruit ices | - |
| gelatins / puddings | 150.00000 |
| granulated sugar | - |
| gravies | - |
| hard candy | - |
| imitation dairy | - |
| instant coffee / tea | - |
| jams / jellies | - |
| meat products | - |
| milk products | - |
| nut products | - |
| other grains | - |
| poultry | - |
| processed fruits | - |
| processed vegetables | - |
| reconstituted vegetables | - |
| seasonings / flavors | - |
| snack foods | - |
| soft candy | 150.00000 |
| soups | - |
| sugar substitutes | - |
| sweet sauces | - |
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Potential Uses
Natural Occurrence
Synonyms
4H-1-
benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-
3-[[(2S,3R,4R,5R)-5-[(1R)-1,2-
dihydroxyethyl]-3,4-dihydroxy-2-oxolanyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1-benzopyran-4-one
3-[(2S,3R,4R,5R)-5-[(1R)-1,2-
dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one
2-(3,4-
dihydroxyphenyl)-3-(b-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-(3,4-
dihydroxyphenyl)-3-(beta-D-glucofuranosyloxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-(3,4-
dihydroxyphenyl)-3-(beta-dextro-glucofuranosyl oxy)-5,7-dihydroxy-4H-1-benzopyran-4-one
2-(3,4-
dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl beta-D-glucofuranoside
alpha-
glycosyl isoquercitrin
3,3',4',5,7-
pentahydroxyflavone 3-b-D-glucofuranoside
3,3',4',5,7-
pentahydroxyflavone 3-beta-D-glucofuranoside
3,3',4',5,7-
pentahydroxyflavone 3-beta-dextro-glucofuranoside
quercetin 3-β-D-glucoside
iso
quercetin, enzymatically modified
iso
quercitrin
iso
quercitroside
sanmelm
trifoliin A
iso
trifolin
PubMed:
Research on the bioactivity of isoquercetin extracted from marestail on bladder cancer EJ cell and the mechanism of its occurrence.
PubMed:
Persimmon (Diospyros kaki L.) leaves: a review on traditional uses, phytochemistry and pharmacological properties.
PubMed:
Neuroprotective Effect of Prenylated Arylbenzofuran and Flavonoids from Morus alba Fruits on Glutamate-Induced Oxidative Injury in HT22 Hippocampal Cells.
PubMed:
Bioprospecting medicinal plants for antioxidant components.
PubMed:
[Study of screening nephroprotective bioactive substances based on triple-color fluorescence probes in Carthami flos].
PubMed:
Identification of phenylpropanoids in fig (Ficus carica L.) leaves.
PubMed:
[Study on chemical constituents from twig and leaf of Juniperus sabina].
PubMed:
Induction of hepatic apolipoprotein A-I gene expression by the isoflavones quercetin and isoquercetrin.
PubMed:
Comparative analysis of antioxidant activity and functional components of the ethanol extract of lotus (Nelumbo nucifera) from various growing regions.
PubMed:
Unconventional approaches to the prevention of cancer associated thrombosis.
PubMed:
Flavonoids from tartary buckwheat induce G2/M cell cycle arrest and apoptosis in human hepatoma HepG2 cells.
PubMed:
Antiplatelet Activity of Morus alba Leaves Extract, Mediated via Inhibiting Granule Secretion and Blocking the Phosphorylation of Extracellular-Signal-Regulated Kinase and Akt.
PubMed:
Thiol isomerases in thrombus formation.
PubMed:
Estimation of flavoniods, antimicrobial, antitumor and anticancer activity of Carissa opaca fruits.
PubMed:
Rosmarinic Acid and Its Methyl Ester as Antimicrobial Components of the Hydromethanolic Extract of Hyptis atrorubens Poit. (Lamiaceae).
PubMed:
Flavonoids with α-glucosidase inhibitory activities and their contents in the leaves of Morus atropurpurea.
PubMed:
Isoquercetin protects cortical neurons from oxygen-glucose deprivation-reperfusion induced injury via suppression of TLR4-NF-кB signal pathway.
PubMed:
First identification of α-glucosidase inhibitors from okra (Abelmoschus esculentus) seeds.
PubMed:
Antioxidant and α-glucosidase inhibitory activities of cucurbit fruit vegetables and identification of active and major constituents from phenolic-rich extracts of Lagenaria siceraria and Sechium edule.
PubMed:
Simultaneous HPLC quantitative analysis of active compounds in leaves of Moringa oleifera Lam.
PubMed:
Cytotoxic evaluation of Melia azedarach in comparison with, Azadirachta indica and its phytochemical investigation.
PubMed:
Anti-H5N1 virus flavonoids from Capparis sinaica Veill.
PubMed:
Syzygium cumini (L.) Skeels: a review of its phytochemical constituents and traditional uses.
PubMed:
Simultaneous Determination of Crypto-Chlorogenic Acid, Isoquercetin, and Astragalin Contents in Moringa oleifera Leaf Extracts by TLC-Densitometric Method.
PubMed:
[Analysis of fingerprint and bioactive components of Bidens biternata by HPLC].
PubMed:
The environmental and human effects of ptaquiloside-induced enzootic bovine hematuria: a tumorous disease of cattle.
PubMed:
1,25-Dihydroxyvitamin D3-glycoside of herbal origin exhibits delayed release pharmacokinetics when compared to its synthetic counterpart.
PubMed:
Complete 1H NMR spectral analysis of ten chemical markers of Ginkgo biloba.
PubMed:
Chemical composition of currant seed extracts and their protective effect on human lymphocytes DNA.
PubMed:
Palynological origin, phenolic content, and antioxidant properties of honeybee-collected pollen from Bahia, Brazil.
PubMed:
Flavonoid compounds identified in Alchemilla L. species collected in the north-eastern Black Sea region of Turkey.
PubMed:
Antidiabetic activity of isoquercetin in diabetic KK -Ay mice.
PubMed:
Synthesis and antiviral activity of substituted quercetins.
PubMed:
Enzymatic Synthesis of the Flavone Glucosides, Prunin and Isoquercetin, and the Aglycones, Naringenin and Quercetin, with Selective α-L-Rhamnosidase and β-D-Glucosidase Activities of Naringinase.
PubMed:
Chemical composition and antioxidant activities of extracts from Apocyni Veneti Folium.
PubMed:
The acute effect of ingesting a quercetin-based supplement on exercise-induced inflammation and immune changes in runners.
PubMed:
Effect of mixed flavonoids, n-3 fatty acids, and vitamin C on oxidative stress and antioxidant capacity before and after intense cycling.
PubMed:
Hepatoprotective effects of methanol extract of Carissa opaca leaves on CCl4-induced damage in rat.
PubMed:
[Simultaneous determination of six flavonoids in Apocynum venetum by HPLC].
PubMed:
A new ursane-type triterpenoid glycoside from Centella asiatica leaves modulates the production of nitric oxide and secretion of TNF-α in activated RAW 264.7 cells.
PubMed:
Comprehensive separation and identification of chemical constituents from Apocynum venetum leaves by high-performance counter-current chromatography and high performance liquid chromatography coupled with mass spectrometry.
PubMed:
Phenolic-containing organic extracts of mulberry (Morus alba L.) leaves inhibit HepG2 hepatoma cells through G2/M phase arrest, induction of apoptosis, and inhibition of topoisomerase IIα activity.
PubMed:
Inhibition of influenza virus replication by plant-derived isoquercetin.
PubMed:
Solvent gradient elution for comprehensive separation of constituents with wide range of polarity in Apocynum venetum leaves by high-speed counter-current chromatography.
PubMed:
Comparative evaluation of quercetin, isoquercetin and rutin as inhibitors of alpha-glucosidase.
PubMed:
Phenylpropanoid glycosides from Heterosmilax erythrantha and their antioxidant activity.
PubMed:
Effects of quercetin and EGCG on mitochondrial biogenesis and immunity.
PubMed:
Study on the interaction between 3 flavonoid compounds and alpha-amylase by fluorescence spectroscopy and enzymatic kinetics.
PubMed:
Simultaneous determination of seven active flavonols in the flowers of Abelmoschus manihot by HPLC.
PubMed:
Level of catechin, myricetin, quercetin and isoquercitrin in buckwheat (Fagopyrum esculentum Moench), changes of their levels during vegetation and their effect on the growth of selected weeds.
PubMed:
Cellular reactive oxygen species inhibitory constituents of Hypericum thasium Griseb.
PubMed:
Flavonoids in onion cultivars (Allium cepa L.).
PubMed:
Calpain inhibitory flavonoids isolated from Orostachys japonicus.
PubMed:
[Chemical constituents of flavonoids from Apocynum venetum].
PubMed:
In vitro activity of uva-ursi against cytochrome P450 isoenzymes and P-glycoprotein.
PubMed:
[Isolation and preparation of flavonoids from the leaves of Nelumbo nucifera Gaertn by preparative reversed-phase high performance liquid chromatography].
PubMed:
Quantitative phytochemical analyses of six hypericum species growing in slovenia.
PubMed:
Determining the binding affinities of phenolic compounds to proteins by quenching of the intrinsic tryptophan fluorescence.
PubMed:
Binding of selected phenolic compounds to proteins.
PubMed:
[Quantitative analysis of active substances in St. John's wort (Hypericum perforatum L.) by the high performance liquid chromatography method].
PubMed:
Constituents of the underground parts of Glehnia littoralis.
PubMed:
[Oxyanthraquinones and flavonoids from garland chrysanthenum].
PubMed:
Hepatoprotective effect of Apocynum venetum and its active constituents.
PubMed:
Quercetin glycosides in Psidium guajava L. leaves and determination of a spasmolytic principle.
PubMed:
Different properties of monomer and heterodimer forms of phosphatidylinositol 3-kinases.